Volume Contents 1995 NUMBER 1 Contents Contributors to this Issue Graphical Abstracts TETRAHEDRON PERSPECTIVE NUMBER 4 F. H. Westheimer Coincidences, decarboxylation, and electrostatic effects ik-Soo Lee, Xianjian Ma, Novel cytotoxic labdane diterpenoids from Neouvaria acuminatissima Hee-Byung Chai, Domingo A. Madulid, R. Brian Lamont, Melanie J. O'Neill, Jeffrey M. Besterman, Norman R. Farnsworth, D. Doel Soejarto, Geoffrey A. Cordell, John M. Pezzuto and A. Douglas Kinghorn Marc M. Greenberg Photochemical release of protected oligonucleotides containing 3'-glycol- ate termini Paul Dowd, Wei Zhang and Cyclobutanone-based tandem free radical rearrangements: formation of Khalid Mahmood bicyclic and tricyclic ketones Haiyin He, Palaniappan Kulanthaivel, New antiproliferative and antiinflammatory 9,11-secosterols from the Bill J. Baker, Kiyomi Kalter, gorgonian Pseudopterogorgia sp. Jim Darges, Divann Cofield, Leslie Wolff and Laurel Adams Timothy D. Lash and Cari P. Denny Porphyrins with exocyclic rings—V. Synthesis of a naphtho[1,2-b]porphyrin Ze-Qi Xu, Ramachandra V. Joshi and Alkylation of adenine with functionalized tert-propargyl carbonates. Jiri Zemlicka Synthesis of 3'-hydroxymethyladenallene—a new analogue of 2'-deoxy- adenosine Dian Chen, Ramunas J. Motekaitis, The synthesis of binucleating polyaza macrocyclic and macrobicyclic 1. Murase and Arthur E. Martell ligands and the dioxygen affinities of their cobalt complexes Albert Padwa, Michael Meske and Synthesis of novel bicyclic nitrogen heterocycles by the intramolecular Zhijie Ni dipolar cycloaddition reaction of nitrones with allenes and alkynes Osamu Tamura, Toshiyuki Okabe, Studies on tandem transesterification and intramolecular cycloaddition of Tatsuya Yamaguchi, Kentoku Gotanda, nitrones—|. Sequential bicyclization of a-methoxycarbonyinitrones with Katsuhide Noe and allyl alcohols Masanori Sakamoto Osamu Tamura, Toshiyuki Okabe, Studies on tandem transesterification and intramolecular cycloaddition of Tatsuya Yamaguchi, Junko Kotani, nitrones—il. Sequential bicyclization of a,a-dialkoxycarbonylnitrones with Kentoku Gotanda and allyl alcohols Masanori Sakamoto 237 Tetrahedron Kaori Ando, Mutsuo Kankake, New building blocks, er a 2,2-dioxides; Takayoshi Suzuki and ———- and their Diels—Alder reaction with dimethyl acetylenedicarb- Hiroaki Takayama oxylate Konstantina Kehagia, The formation of B-lactam derivatives and a C,-symmetrical heterocycle Alexander Démling and Ivar Ugi from 5,6-dihydro-2H-1 ,3-oxazines Arndt Brandes and H. M. R. Hoffmann Diastereoselective synthesis of functionalized 9-ring ethers (oxonins) H. M. R. Hoffmann and Arndt Brandes Stereoconvergent synthesis of enantiopure (—)-trans-lauthisan. Building kit for medium ring oxacycle construction and _contrathermodynamic epimerization at allylic carbon C(8) via ‘invisible’, E-configurated medium ring olefin P. Delair, C. Einhorn, J. Einhorn and New f-amino alcohols derived from t-valine as chiral inductors for J. L. Luche enantioselective reductions of, and nucleophilic additions to carbonyl compounds Xin-Jie Chu, Hong Dong and Total synthesis of chromomoric acid B and F methyl esters Zhi-Yu Liu Tse-Lok Ho and Po-Fei Yang Synthesis of phenolic sesquiterpenes via oxidative cleavage of benzo- cycloalkenols Chin-Kang Sha, Ren-Sheng Lee and Synthesis and Diels—Alder reactions of furo[2,3-c]pyrroles and benzofuro- Yu Wang [2,3-c]pyrroles David C. Horwell, William Howson, The design of dipeptide helical mimetics—|. The synthesis of 1,6-disub- William P. Nolan, Giles S. Ratcliffe, stituted indanes David C. Rees and Henriette M. G. Willems Paolo Scrimin, Paolo Tecilla and Chiral lipophilic ligands—!. Cu(Il)-Mediated transport of a-amino acids Umberto Tonellato across a bulk chloroform membrane Albert Guijarro and Miguel Yus DTBB-Catalysed lithiation of 1,4-dichloro-2-butyne under Barbier conditions: synthesis of functionalised alkynes Pedro Victory, Angel Alvarez-Larena, A non-obvious reaction pathway in the formation of 2-aminobenzene-1,3- Gabriel Germain, Raoul Kessels, dicarbonitriles from a,B-unsaturated ketones or aldehydes Joan F. Piniella and Anton Vidal-Ferran Dennis P. Piet, Adriaan J. Minnaard, Biotransformation of (+)-4,8-dimethylcyclodeca-3(E),7(E)-dien-1B-ol and Karel A. van der Heyden, (+)-hedycaryol by Cichorium intybus Maurice C. R. Franssen, Joannes B. P. A. Wijnberg and Aede de Groot Namakkal G. Ramesh and Mitsunobu reaction of 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxy- Kalpattu K. Balasubramanian methyl-hex-1-enitols and 1,5-anhydro-2-deoxy-4,6-O-protected-hex-1- enitols. A novel method for the synthesis of 2-C-methylene glycosides and a useful alternative to Ferrier rearrangement Darrin A. Barr, Michael J. Dorrity, X=Y-ZH Compounds as potential 1,3-dipoles—XLIll. Metal ion catalysed Ronald Grigg, Simon Hargreaves, asymmetric 1,3-dipolar cycloaddition reactions of imines and menthyl John F. Malone, John Montgomery, acrylate James Redpath, Paul Stevenson and Mark Thornton-Pett Ronald Grigg, Visuanathar Sridharan, Sequential and cascade 1,3-dipolar cycloaddition—palladium catalysed Selvaratnam Suganthan and carbonylation—cyclisation reactions. Diastereospecific and homochiral Andrew W. Bridge processes Luis F. Garcia-Alles and Vicente Gotor Synthesis of 5'-O- and 3'-O-nucleoside carbamates Ben-Ami Feit, Sarit Shapira and A hydride transfer reaction from salts of carbanions to activated olefins Amatzya Herbst A. Papchikhin, P. Agback, J. Plavec The diastereospecific synthesis of new 2',3'-cis-a-fused carbocyclic and J. Chattopadhyaya nucleosides Instructions to Contributors Tetrahedron NUMBER 2 Contents TETRAHEDRON SYMPOSIA-IN-PRINT NUMBER 56 MOLECULAR RECOGNITION Guest Editor: ANDREW D. HAMILTON Department of Chemistry, University of Pittsburgh, Pittsburgh, USA Contributors to this Issue Announcement: Tetrahedron Symposia-in-Print Preface Graphical Abstracts Yasuhiro Aoyama, Yuki Imai, Ken Endo Use of supramolecular cavities maintained by hydrogen-bonded network and Kenji Kobayashi in molecular crystals as a novel binding site for guests in water. The solid- state host-guest complexation of a bisresorcinol derivative of anthracene Denise M. Perreault, Xiaohong Chen The advantages of using rigid polyaza-clefts for hydrogen-bonding and Eric V. Anslyn molecular recognition Daniel L. Beckles, James Maioriello, Complexation of creatinine by synthetic receptors Vincent J. Santora, Thomas W. Bell, Eddy Chapoteau, Bronislaw P. Czech and Anand Kumar Ronald Breslow, Sherin Halfon and Molecular recognition by cyclodextrin dimers Biliang Zhang Gilles Vériot, Jean-Pierre Dutasta, Synthesis of C3-cyclotriveratrylene ligands for iron(Il) and iron(II!) coordin- Galina Matouzenko and André Collet ation Blake R. Peterson, Peter Wallimann, Steroid complexation by cyclophane receptors in aqueous solution: Daniel R. Carcanague and substrate selectivity, enthalpic driving force for cavity inclusion, and Francois Diederich enthalpy—entropy compensation Servando Mufioz, Ernesto Abel, Control of vesicle formation by chemical switching Keshi Wang and George W. Gokel Paolo Tecilla, Vrej Jubian and Synthetic hydrogen bonding receptors as models of transacylase enzymes Andrew D. Hamilton Heather A. Carison and Investigations into the stereochemistry of cyclophane—steroid complexes William L. Jorgensen via Monte Carlo simulations Tadashi Mizutani, Tadashi Ema and Restricted internal rotation of amino acid esters. Quantitative evaluation of Hisanobu Ogoshi rigidity of a molecule in terms of internal rotation entropy Roland J. Pieters, lvan Huc and Reciprocal template effects in bisubstrate systems: a replication cycle Julius Rebek, Jr Willem Verboom, Paul J. Bodewes, A novel approach to inherently chiral calix[4jarenes by direct introduction Georget van Essen, Peter Timmerman, of a substituent at the meta position Gerrit J. van Hummel, Sybolt Harkema and David N. Reinhoudt R. Stephen Wylie and Modelling the influence of porphyrin supermacrocycles on the kinetics of Jeremy K. M. Sanders bimolecular reactions Tetrahedron Paolo Scrimin, Paolo Tecilia, Metal ions co-operativity in the catalysis of the hydrolysis of a B-amino Umberto Tonellato, Giovanni Valle and ester by a macrocyclic dinuclear Cu(Il) complex Andrea Veronese Viadimir Kral and Jonathan L. Sessler Molecular recognition via base-pairing and phosphate chelation. Ditopic and tritopic sapphyrin-based receptors for the recognition and transport of nucleotide monophosphates Tony D. James, Hirosuke Kawabata, Cholesterol as a versatile platform for chiral recognition Rainer Ludwig, Kazutaka Murata and Seiji Shinkai Seung Soo Yoon and W. Clark Still Sequence-selective peptide binding with a synthetic receptor Oldrich Kocian, Neil Spencer, Self-assembly in the metallation of bis(aminoaryl) ethers J. Fraser Stoddart, lan Cragg-Hine, Matthew Davidson, Francis S. Mair, Paul Raithby, Ronald Snaith, Thomas Kottke and Ehmke Pohl Alessandro Casnati, Paola Jacopozzi, Bridged calix[6Jarenes in the cone conformation: new receptors for quater- Andrea Pochini, Franco Ugozzoli, nary ammonium cations Roberta Cacciapaglia, Luigi Mandolini and Rocco Ungaro A. Arduini, M. Cantoni, E. Graviani, Gas-phase complexation of neutral molecules by upper rim bridged A. Pochini, A. Secchi, A. R. Sicuri, calix[4jarenes R. Ungaro and M. Vincenti Eric E. Simanek, Mathai Mammen, Design and synthesis of hydrogen-bonded aggregates. Theory and Dana M. Gordon, Donovan Chin, computation applied to three systems based on the cyanuric acid— John P. Mathias, Christopher T. Seto melamine lattice and George M. Whitesides Craig S. Wilcox, Eun-il Kim, Experimental and theoretical studies of substituent effects in hydrogen David Romano, Lung Huang Kuo, bond based molecular recognition of a zwitterion by substituted arylureas Arthur L. Burt and Dennis P. Curran Thomas J. Murray, Synthesis of heterocyclic compounds containing three contiguous Steven C. Zimmerman and hydrogen bonding sites in all possible arrangements Sergei V. Kolotuchin Instructions to Contributors NUMBER 3 Contents Contributors to this Issue Graphical Abstracts Tuck C. Wong, Luis R. Collazo and 14N and '5N NMR studies of highly sterically hindered tertiary amines Frank S. Guziec, Jr Seung-Yong Choi and Picosecond radical kinetics. Alkoxycarbonyl accelerated cyclopropyl- Martin Newcomb carbinyl radical ring openings Paul Galatsis and Jeffrey J. Manwell Construction of fused bicyclic cyclooctane ring frameworks Masahiko Taniguchi, Hideaki Fujii, Stereoselective reduction of «,B-epoxy ketones with sodium borohydride in Koichiro Oshima and Kiitiro Utimoto the presence of calcium chloride or lanthanum chloride. A practical preparation of erythro-a.,B-epoxy alcohols Kaoru Nakamura, Shin-ichi Kondo, Mechanistic study for stereochemical control of microbial reduction of a- Nobuyoshi Nakajima and keto esters in an organic solvent Atsuyoshi Ohno Hiroshi Oda, Tohru Kobayashi, Synthesis of 5,12-DiHETE derivative by palladium-catalyzed ternary Masanori Kosugi and Toshihiko Migita coupling between vinylic halide, a vinylic tin compound, and norbornadiene Tetrahedron Tsuyoshi Satoh, Yasuhiro Mizu, Ligand exchange reaction of sulfoxides in organic synthesis: a new Taku Kawashima and Koji Yamakawa synthesis of a-chloroketones from carbonyl compounds with one-carbon homologation Peter Metz, Michael Fleischer and Intramolecular Diels-Alder reaction of vinylsulfonates derived from Roland Froéhlich hydroxyalkyl substituted 1,3-dienes and oxidative desulfurization of the resultant sultones Regina Thiergardt, Grety Rihs, Cladospirone bisepoxide: definite structure assignment including absolute Paul Hug and Heinrich H. Peter configuration and selective chemical transformations Jazid Kabbara, Steffen Flemming, Copper-catalyzed conjugate addition of trialkylaluminium to o,B-unsaturat- Klaus Nickisch, Harribert Neh and ed carbonyl compounds Jiirgen Westermann Alexander Démling, Angela Bayler and 2,5-Dihydro-4-hydroxymethyl-1,3-oxazoles by Asinger condensation Ivar Ugi Natalia B. Dyatkina, Fritz Theil and Stereocontrolled synthesis of the four stereoisomeric diphosphorylphos- Martin von Janta-Lipinski phonates of carbocyclic 2',3'-dideoxy-2',3'-didehydro-5'-noradenosine Alois Fiirstner and Andreas Ernst Syntheses of camalexin, indolopyridocoline and flavopereirine Upul K. Bandarage, Lyall R. Hanton Synthesis and structural characterization of dithiacyclophanes derived and Robin A. J. Smith from biaryldithiols Ecaterina Roth, Janina Altman, Amidoalkylation of aromatics with glyoxylic acid-y-lactam adducts: 2- Moshe Kapon and Dov Ben-ishai pyrrolidinone, pyroglutamic acid amide and ester Andrew Pelter and The chemistry of organoborates—IX. A regiospecific and highly stereo- M. Eamon Colclough selective construction of trisubstituted af-unsaturated ketones, tetrasub- stituted af-unsaturated ketones and specifically protected 1,3-diketones from alkynyltrialkylborates Jacek Grodner and Marek Chmielewski Synthesis of (6A) 4-tbutoxycarbonyl-7-hydroxymethyl-1-oxa-3-cephem from b-arabinal Benjamin Rodriguez, Rearranged neo-clerodane diterpenoids from Teucrium brevifolium and Maria C. de la Torre, Maria L. Jimeno, their biogenetic pathway Maurizio Bruno, Caterina Fazio, Franco Piozzi, Giuseppe Savona and Aurea Perales Amuri Kilonda, Elisabeth Dequeker, Synthesis of a chiral 2,6-bridged morpholine system: trans-6,7-diol Frans Compernolle, Pieter Delbeke, derivatives of 8-oxa-3-azabicyclo[3.2.1]octane Suzanne Toppet, Babady-Bila and Georges J. Hoornaert Maurizio Fagnoni, Mariella Mella and Alkylation of alkenes by radicals generated through photoinduced single Angelo Albini electron transfer Stephen Husbands, William Fraser, Latent inhibitors—XI. The synthesis of 5-spirocyclopropyl dihydroorotic Colin J. Suckling and acid Hamish C. S. Wood oe manne Pakulski and The reaction of acetyliron Jin®-CsHs)Fe(CO)(PPhs)(COCHs)] with sugar Aleksander Zamojski aldehydes. New synthesis of deoxysugars Nasser lIranpoor and Peyman Salehi Ceric ammonium nitrate: a mild and efficient reagent for conversion of epoxides to B-nitrato alcohols Hashem Sharghi and Hossein Eshghi Efficient synthesis of macrocyclic diamides M. Angeles Pradera, José L. Molina Synthesis of diisothiocyanato derivatives of disaccharides and José Fuentes José M. Blanco, Olga Caamafio and Chiral sulfinic acids: synthesis of sodium (15S,2S,5A)-2-isopropyl-5- Franco Fernandez methyicyclohexanesulfinate by a novel route pee ge G. Haraldsson, The synthesis of homogeneous triglycerides of eicosapentaenoic acid and Birgir O.G udmundsson and docosahexaenoic acid by lipase Orn Almarsson Bo-Long Poh and Chi Ming Tan Crown ethers as guests of cyclotetrachromotropylene in water Tetrahedron M. Pilar Vazquez-Tato, Julio A. Seijas, Synthesis of (3S,55S)-quinuclidine-3,5-diol and of [3S-(3a,3aa,7aa)]- George W. J. Fleet, octahydro-2-furo[2,3-c]pyridinol from b-arabinose Christopher J. Mathews, Philippa R. Hemmings and David Brown Instructions to Contributors NUMBER 4 Contents Contributors to this Issue Graphical Abstracts TETRAHEDRON REPORT NUMBER 364 Andreas Heumann and Marius Réglier The stereochemistry of palladium-catalysed cyclisation reactions—B. Addition to n-allyl intermediates John W. Huffman, W. Kenneth Banner, Stereoselective synthesis of the epimeric A7-tetrahydrocannabinols Grace K. Zoorob, H. Howard Joyner, Patricia H. Reggio, Billy R. Martin and David R. Compton Xinhua Qian, K. C. Russell, Stereoselective total ae of topographically constrained designer Lakmal W. Boteju and Victor J. Hruby amino acids: 2',6'-dimethyl-B-methyltyrosines Tai-Shun Lin, Mei-Zhen Luo and Synthesis of several pyrimidine t-nucleoside analogues as potential Mao-Chin Liu antiviral agents Alan R. Katritzky, Clara N. Fali and Addition reactions of immonium benzotriazolates to acetylenic esters Daniela C. Oniciu Nilsa R. Graciani, Daniel S. Swanson Phosphomonoesters and phosphodiesters derived from the photohydro- and Jeffery W. Kelly lysis of 2-methoxy-5-nitrophenyl substituted phosphotriesters Carlos M. Cerda-Garcia-Rojas and Cyclic hemiketals from the sponge Raspailia (Raspaxilla) sp. D. John Faulkner Dewey G. McCafferty, Synthesis of redox derivatives of lysine and their use in solid-phase Barney M. Bishop, Craig G. Wall, synthesis of a light-harvesting peptide Solon G. Hughes, Sandra L. Mecklenberg, Thomas J. Meyer and Bruce W. Erickson Osamu Shirota, Hiroshi Morita, Structures of xuxuarines, stereoisomeric triterpene dimers from Maytenus Koichi Takeya and Hideji Itokawa chuchuhuasca Hiroshi Morita, Shinji Nagashima, Structures and conformation of antitumour cyclic pentapeptides, astins A, Koichi Takeya, Hideji Iltokawa and B and C, from Aster tataricus Yoichi litaka Takahisa Machiguchi Synthesis and isolation of tropothione: a comparative study of spectral property with tropone Shigetoshi Kadota, Jian Xin Li, Constituents of cimicifugae rhizoma—ll. Isolation and structures of new Ken Tanaka and Tsuneo Namba cycloartenol triterpenoids and related compounds from Cimicifuga foetida ta Paul Wiedenau, Barbara Monse and Total synthesis of (+)-cis-trikentrin A Siegfried Blechert Regine Haftendorn and Synthesis of 2-modified 1,3-diacylglycerols Renate Ulbrich-Hofmann Tetrahedron Wilhelm Karnbrock, Enantioselective synthesis of S-o-carboranylalanine via methylated bis- Hans-Jiirgen Musiol and Luis Moroder lactim ethers of 2,5-diketopiperazines Colin Granier and Roger Guilard First unequivocal synthesis of 1 or 8-N-monosubstituted 1,4,8,12-tetra- azacyclopentadecane Mouad Alami, Sylvie Gueugnot, An efficient synthesis of 1,3(E),5(2Z), 1,3(E),5(E) and 1,3(Z),5(Z)-trienes: Elisa Domingues and application to the synthesis of galbanolenes and (92Z,11&)-9,11,13- Gérard Linstrumelle tetradecatrien-1-yl acetate Philippe Rasoanaivo, A new group of isoquinoline dimers from Hernandia voyronii Suzanne Ratsimamanga-Urverg, Corrado Galeffi, Marcello Nicoletti, Francois Frappier and Marie-Thérése Martin Pascal Munier, Aniela Krusinski, Stéréosélectivité comparée de la réduction de trifluorométhylcétones et Dominique Picq et Daniel Anker des méthyicétones correspondantes: nouvelles voies d'accés a des dérivés trifluorométhylés de pentoses B. Cathala, C. Picard, L. Cazaux, Macrocyclic dilactams with pendant acidic functions as discriminating P. Tisnés and M. Momtchev agents for lanthanide ions Blanca Ocana, Modesta Espada and Reactions of aza- and diazaanthraquinone N-oxides Carmen Avendafo Mercedes Villacampa, Regioselective synthesis of 1,8-diazaanthracene-9,10-dione by tandem Elena de la Cuesta and directed ortho-metallation/metal—halogen exchange Carmen Avendano Pedro Molina, Aurelia Pastor, Vinyliminophosphorane-mediated preparation of 2-aryiquinoline and 4- Maria Jesus Vilaplana and aryl-1-azaanthraquinone derivatives. X-Ray crystal structure of 1,2- Concepcién Foces-Foces dihydro-3H-indazolo[2,3-a]quinolin-4-one Marcello Tiecco, Lorenzo Testaferri, Selenium-induced cyclization of O-allyl oximes as a synthetic route to N- Marco Tingoli, Luana Bagnoli and alkyl isoxazolidines Claudio Santi Philip C. Bulman Page, Enolate bromination in 2-acyl-1,3-dithiane 1-oxides Michael J. McKenzie, Steven M. Allin, Eric W. Collington and Robin A. E. Carr Carlos Cativiela, José |. Garcia, The use of heterogeneous catalysis in Diels—Alder reactions of N-acetyl- José A. Mayoral, Elisabet Pires, a, B-dehydroalaninates Ana J. Royo and Francois Figueras Shamil Latypov, Rogelio Fernandez, The conformation of aldisin and analogues. A potential model for expand- Emilio Quinoa and Ricardo Riguera ed nucleosides Tetrahedron Reports on Organic Chemistry Instructions to Contributors NUMBER 5 Contents iii Contributors to this Issue Vv Graphical Abstracts 1311 Corrigendum Harold Hart and Perumal Rajakumar 1313 2'-Substituted meta-terphenyls as building blocks for cyclophanes with intra-annular functionality George A. Kraus, Danette R. Vines and 1337 Conjugate addition reactions of metallated alkyl pyridines. A direct route to John H. Malpert 6-substituted pyridones Heinrich Becker, Marcos A. Soler and 1345 Selective asymmetric dihydroxylation of polyenes K. Barry Sharpless Tetrahedron Hiroshi Suginome, Atsushi Konishi, Photoinduced molecular transformations—CLVI. New photoadditions of 2- Hideo Sakurai, Hiroki Minakawa, hydroxy-1,4-naphthoquinones with naphthols and their derivatives Toshihiro Takeda, Hisanori Senboku, Masao Tokuda and Kazuhiro Kobayashi Hiromi Sano, Shigeru Mio, Stereocontrolied synthesis of spirosuccinimide derivative of (+)-hydanto- Naoto Tsukaguchi and Soji Sugai cidin Denis Planchenault, Robert Dhal and New agents of biaryl oxidative coupling in fluoro acid medium—vVI. Jean-Pierre Robin Application to the synthesis of phenolic bisbenzocyclooctadiene lignans M. R. Maziéres, V. D. Romanenko, New diaza pentadienylium salts (cyanine dyes) derived from N-silylated A. O. Gudima, C. Payrastre, phosphinimines and guanidines M. Sanchez and J. G. Wolf P. Macours, J. C. Braekman and Concise asymmetric syntheses of (+)- and (—)-tetraponerine-8, (+)- and D. Daloze (—)-tetraponerine-7, and their ethyl homologues. A correction of the structures of tetraponerine-3 and -7 Zhi-cai Yang and Wei-shan Zhou Asymmetric total synthesis of (+)-goniotriol and (+)-goniofufurone Arun N. Dixit, K. Venodhar Reddy, Conformational preferences of a-functionalised keten-S,N-acetals: potent- Abdul Rakeeb A. S. Deshmukh, ial role of S..O and S..S interactions in solution Srinivasachari Rajappa, Bishwajit Ganguly and Jayaraman Chandrasekhar Francesc Rabanal, Ernest Giralt and Synthesis and applications of a new base-labile fluorene derived linker for Fernando Albericio solid-phase peptide synthesis Sanjib Bera, Tanmaya Pathak and Opening of 2',3'-O-anhydro ring of 2',3'-O-anhydro-/yxo-uridine by alkyl- Graham J. Langley and arylamines. Easy syntheses and preparative uses of 2'-deoxy-2'-alkyl- amino-xylo- and 3'-deoxy-3'-alkylamino-ara-uridines Luc Van Meervelt, Structure and properties of phosphonium ylides—betaines, derivatives of 2- Geertrui S. Schuerman, phenyl-2-oxazolin-5-one and its thio- and seleno-analogues Viadimir S. Brovarets, Nikolai |. Mishchenko, Evgenii A. Romanenko and Boris S. Drach Ganesh Pandey and Enyne cyclisation by photoinduced electron transfer (PET) promoted in B. B. V. Soma Sekhar situ generated electrophilic selenium species: a new carbocyclisation strategy Susana Puertas, Francisca Rebolledo Selective ammonolysis and aminolysis of dimethyl succinate. Synthesis of and Vicente Gotor optically active N-alkyisuccinimides Félix Busqué, Pedro de March, Synthesis of some new highly functionalized C,-synthons Marta Figueredo and Josep Font Martin C. Clasby, Donald Craig, Intramolecular Diels-Alder reactions of internally-substituted trienylsulf- Alexandra M. Z. Slawin, ones. Synthesis of bicyclo[4.3.0] and -[4.4.0] systems possessing a bridge- Andrew J. P. White and head sulfonyl group David J. Williams Instructions to Contributors Tetrahedron NUMBER 6 Contents Contributors to this Issue Graphical Abstracts Corrigendum TETRAHEDRON REPORT NUMBER 365 John P. Richard A consideration of the barrier for carbocation—nucleophile combination reactions Scott A. Petrich, Fred A. Hicks, The application of vinylogous iminium salts and related synthons to the Doug R. Wilkinson, James G. Tarrant, preparation of trisubstituted pyridines Steve M. Bruno, Marian Vargas, Kirsten N. Hosein, John T. Gupton and James A. Sikorski Serkos A. Haroutounian and 4'-Hydroxystyryldiazines: synthesis and fluorescence properties John A. Katzenellenbogen Krzysztof E. Krakowiak, One- and two-step metal ion templated syntheses of the cryptands Jerald S. Bradshaw, Xiaolan Kou and N. Kent Dalley Darren L. Holmes and Synthesis and acidity constants of 'SCO,H-labelled mono and dipyrrole David A. Lightner carboxylic acids. pK, from 3C NMR Werner Tochtermann, Stefan Bruhn, Synthese stereoisomerer 4,7-Epoxy-hydroazulen-5,6-dicarbonsauredime- Martin Meints, Christian Wolff, thylester mit Lactaran-Gerist Eva-Maria Peters, Karl Peters und Hans Georg von Schnering G. Galley, M. Patzel and P. G. Jones Diastereofacial selectivity of the cycloaddition of diazo compounds to enones Tawfik Gharbaoui, Michel Legraverend, Synthesis of new carbocyclic oxetanocin analogues Odile Ludwig, Emile Bisagni, Anne-Marie Aubertin and Lyubov Chertanova Michéle Saniére, Isabelle Charvet, Enantiopure hydroxylactones from L-ascorbic and D-isoascorbic acids—. Yves Le Merrer and Synthesis of (—)-muricatacin Jean-Claude Depezay Christine Gravier-Pelletier, Enantiopure hydroxylactones from L-ascorbic and D-isoascorbic acids—ll. Yves Le Merrer and Synthesis of (—)-(5A,6S)-6-acetoxy-5-hexadecanolide and its diastereo- Jean-Claude Depezay mers Bernard Barlaam, Jean Boivin, A short total synthesis of estrone derivatives: a novel 1,3-rearrangement of Laurent Elkaim, Sarah Elton-Farr and an allylic nitro group Samir Z. Zard Jean-Michel Roulet, Pierre Vogel, Competition between cheletropic and homocheletropic additions of sulfur Frank Wiesemann and dioxide to 2,3,5,6-tetrakis(methylene)bicyclo[2.2.njalkanes. Crystal and A. Alan Pinkerton molecular structures of two 3-thiabicyclo[3.1.0]nexane 3,3-dioxide deriva- tives Jean-Pierre Praly, Djiennane Senni, Synthesis and structure of bromo glycosy! imines readily obtained from René Faure and Gérard Descotes protected glycosyl azides Joél Touet, Laurent Faveriel et Agents de dédoublement—ll. Ethers benzyliques du (A)-(—)- et du (S)-(+)- Eric Brown 2-aminobutan-1-ol, et leur utilisation dans le dédoublement de dérives N- acylés de la phényiglycine et de la p-hydroxyphényiglycine Tetrahedron Tomasz Janecki, Ryszard Bodalski, Horner—Wadsworth-Emmons olefination of nonstabilized phosphonates. A Michat Wieczorek and Grzegorz Bujacz new synthetic approach to B,y-unsaturated amides Hari Babu Mereyala and Stereoselective synthesis of rare (D and L) mono and disaccharides of 5- Sreenivasulu Guntha deoxy hexofuranosiduronic acids by a facile intramolecular rearrangement of hemiacetal heptanolactone alcohols Alicia Marcos, Carmen Pedregal and Synthesis of 1,5- and 1,8-diazaanthraquinones by reaction of aminoquino- Carmen Avendanio linequinones with B-dielectrophiles Antonio Guarna, Ernesto G. Occhiato, Baker's yeast reduction of prochiral y-nitroketones: enantioselective Laura M. Spinetti, Maria E. Vallecchi synthesis of (S)-4-nitroalcohols and Dina Scarpi Alexey V. Tkachev, Reaction of certain a,B-unsaturated terpenic oximes with sodium nitrite in Andrey M. Chibiryaev, acetic acid: a facile synthesis of allylic nitro compounds Alexey Yu. Denisov and Yuri V. Gatilov Adusumilli Srikrishna, Application of microwave heating technique for rapid synthesis of y,5- Sankuratri Nagaraju and unsaturated esters Paturu Kondaiah Giulia Cabella, Giancarlo Jommi, Alkylation of chiral phosphonoglycine equivalents: asymmetric synthesis of Roberto Pagliarin, Guido Sello and diethyl a-amino-a-alkyl-phosphonates Massimo Sisti A. Dominguez, N. Cabezas, Chemoselectivity of chemically modified a-chymotrypsin J. M. Sanchez-Montero and J. V. Sinisterra Julio G. Urones, Isidro S. Marcos, Chemistry of zamoranic acid—|lX. Homochiral synthesis of polygodial and Belen Gomez Pérez, Anna M. Lithgow, warburganal from 17-acetoxy-7-labden-15-ol David Diez, Patricio M. Gémez, Pilar Basabe and Narciso M. Garrido Instructions to Contributors NUMBER 7 Contents Contributors to this Issue Graphical Abstracts Masami Okabe and Ruen-Chu Sun Improved synthesis of 2-amino-5-chlorophenyl-2'-pyrrylketone, a key intermediate in the synthesis of HIV Tat-antagonists Derek H. R. Barton, Ching-Yuh Chern The invention of radical reactions—XXXIV. Homologation of carboxylic and Joseph Cs. Jaszberenyi acids to a-keto carboxylic acids by Barton-ester based radical chain chemistry Derek H. R. Barton, Kari A. D. Swift and The synthesis of 1-hydroxy-3-phenylsulphonylpiperidine-2-thione deriva- Catherine Tachdjian tives utilizing methylthiothiocarbonylation as the key original step Hideyuki Shinmori, Masayuki Takeuchi Spectroscopic sugar sensing by a stilbene derivative with push (Me,N-)- and Seiji Shinkai pull ((HO),B-—)-type substituents Takashi Okano, rst Takakura, A facile preparation method for a,a-difluoroalkanecarboxylic acids and Yuko Nakano, Asako Okajima and esters. A formal difluoromethylene insertion to alkanecarboxylic acids Shoji Eguchi using radical reaction Andreas Gypser, Christiane Bilow and Determination of the absolute configuration of annonin |, a bioactive Hans-Dieter Scharf natural acetogenin from Annona squamosa Astrid Donnerstag, Susanne Marzian, A structurally and biogenetically interesting moenomycin antibiotic Dietrich Miller, Peter Weizel, Dirk Béttger, Andreas Stark, Hans-Wolfram Fehihaber, Astrid Markus, Yveline van Heijenoort and Jean van Heijenoort